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The Top 10 Best Boston Rappers of All Time

Boston, often shadowed by the colossal hip hop scenes of cities like New York, Los Angeles, and Atlanta, has its own vibrant, multifaceted rap scene that brims with talent. The city’s rich and diverse cultural history has fostered a wealth of artists who not only continue to shape Boston’s music identity but also influence the global rap landscape.

From those that broke ground in the genre’s early years to modern visionaries pushing its boundaries, Boston’s roster of rappers is as varied as it is impressive. Whether we’re talking about the streetwise narratives of Cousin Stizz and the bold genre-bending style of BIA, or the enduring impact of stalwarts like Ed O.G. and Big Shug, Boston’s hip hop scene has always been teeming with talent. The city has also gifted the world with legends such as Guru, whose insightful lyricism and innovative approach helped shape hip hop’s golden age, as well as young talent like BIA who are helping push forward the city’s reputation as a thriving rap hub.

Meanwhile, Boston hip hop artists like M-Dot and Akrobatik continue to uphold the city’s rap tradition, infusing it with their own distinct flavors. Whether it’s Esoteric’s thrilling comic-book-laced rhymes or Mr. Lif’s potent socio-political commentary, Boston’s hip-hop lineage offers a refreshing diversity of voices, each echoing a unique facet of the city’s dynamic culture.

So let’s get into it. From Guru, Big Shug and Ed O.G., to Cousin Stizz, M-Dot and Esoteric, here are the top 10 best Boston rappers of all time.

10. BIA

Discography: Nice Girls Finish Last: Cuidado (2018), For Certain (2020)

Born in the city’s neighbourhood of Medford, Massachusetts, BIA is one of the younger rappers from Boston on this list. A natural-born rap star with a fiercely original voice, the MC-singer seamlessly bends genres — from trap to R&B — to fit her sonic vision. Her eclectic mix of hip-hop and Latin influences has redefined Boston’s music scene, infusing it with a fresh flavor. Sharing the microphone with industry greats such as Nicki Minaj and J. Cole, she effortlessly proves her worth with a diverse range of rhythms and vocal deliveries, presenting a new version of herself in each song.

9. M-Dot

Discography: Run MPC (2010), EgO anD The EneMy (2017), Dining In Dystopia (2022), A Dissolute Paradise (EgO anD The EneMy 2) (2023)

Far from the spotlight of commercial hip-hop, M-Dot embodies Boston’s thriving underground rap culture. After getting his big break while touring in Europe as an opener for Krumb Snatcha (of Gang Starr fame) during the 2000s, the underground Boston rapper has been a stalwart of the city’s fine reputation for lyricism and authentic hip hop. His command over language and narrative brings a technical depth to his music, reflecting on both personal experiences and societal issues. A standard-bearer for Boston’s underground rap scene, M-Dot has garnered international respect, and in his complex lyrics and rhythm, the spirit of Boston’s streets is vividly echoed.

8. Slaine

Discography: A World with No Skies (2011), The Boston Project (2013), The King of Everything Else (2014), One Day (2019), The Things We Can’t Forgive (2021)

Born in Boston and raised on the likes of Beastie Boys, LL Cool J, and Kool Moe Dee, rapper-actor Slaine moved to New York to pursue his passion for hip hop. As an MC, Slaine brings a raw, unflinching authenticity to Boston’s hip hop landscape. Known for his work with La Coka Nostra and Special Teamz, Slaine’s tracks bear the marks of his life’s trials and triumphs, resonating with a wide audience. The Boston MC’s unique cinematic approach to rap, nurtured by his acting career — Slaine has appeared in films like Gone Baby Gone and The Town — gives his music an engaging depth. As an artist who continues to push boundaries, Slaine’s influence on Boston’s hip hop scene is both indelible and profound.

7. Cousin Stizz

Discography: One Night Only (2017), Trying to Find My Next Thrill (2019), Just For You (2022)

The city’s first hip hop artist to be crowned Artist of the Year at the Boston Music Awards, Cousin Stizz has spent the past few years making a case of himself as one of the best rappers to emerge from Massachusetts. Cousin Stizz channels Boston’s underrepresented neighborhoods in his rhythmic narratives. His music, marked by an eloquent streetwise lyricism and catchy beats, strikes a chord with a broad audience — whether he’s collaborating with G-Eazy, Offset, or Buddy. Stizz’s authenticity, combined with his knack for storytelling, gives listeners a fresh perspective on the city’s diverse experiences. He’s a true game-changer, reshaping the city’s rap scene with every verse he delivers, and absolutely one of the best Boston rappers in the game today.

6. Mr. Lif

Discography: I Phantom (2002), Mo’ Mega (2006), I Heard It Today (2009), Don’t Look Down (2016).

A member of the Boston rap group, The Perceptionists — along with Akrobatik, and DJ Fakts One — Mr. Lif has been a part of the city’s rap scene for the past two decades. Influenced by legendary ’80s rappers like Chuck D, KRS-One, and Rakim, the Boston MC has the local hip hop scene with his philosophical lyricism and socio-political commentary. His unconventional approach to hip-hop, characterized by thought-provoking narratives and a deep-seated intellect, sets him apart in Boston’s vibrant rap panorama. With The Perceptionists as well as his own solo work, Mr. Lif’s influential raps serves as a testament to the power of hip hop as a tool for social discourse.

5. Esoteric

Discography: Too Much Posse (2006), Egoclapper 2007), Esoteric Vs. Gary Numan (2007), Esoteric Vs. Japan (2008), Serve or Suffer (2009), Saving Seamus Ryan (2009), Fly Casualties (2010), Boston Pharaoh (2011), Machete Mode (with Stu Bangas) (2013).

A veteran of Boston’s underground hip hop scene, Esoteric is renowned for his intricate lyricism and enduring impact. As one half of the rap duo, 7L & Esoteric, a third of Czarface, and a member of underground rap collectives Army of the Pharaohs and Demigodz, Esoteric has been waving the flag for gritty, lyricism-driven hip hop for the past two decades. His razor-sharp rhymes, filled with comic book references and clever metaphors, make Esoteric’s music a thrilling journey for the listener. A flag-bearer of dope rhymes, he represents a unique facet of Boston’s musical identity, emphasizing creativity and individuality.

4. Akrobatik

Discography: Balance (2003), Absolute Value (2008), Built to Last (2014)

Known for his fiercely conscious rap and being a member of The Perceptionists, Akrobatik is a stalwart in Boston’s rap game, unafraid to venture into political and social arenas with his lyrics. His strong yet agile flow, akin to his stage name, is instantly recognizable. A Boston native, he has used his art to convey potent messages about the realities of urban life, ensuring the city’s stories get told in an honest, compelling fashion. A consummate MC, Akrobatik’s prowess on the mic underlines Boston’s penchant for producing hip hop talents of substance.

3. Big Shug

Discography: Never Say Die: The Pre-Album (2005), Who’s Hard? (2005), Street Champ (2007), Otherside of the Game (2008), I.M. 4-EVA (2012), Triple OGzus (2015), The Diamond Report (2019)

A titan in the Boston rap scene, Big Shug’s contributions are not only immense but are also characterized by their enduring impact. A founding member of the Gang Starr Foundation alongside the late Guru, Shug’s deep, gravelly voice and no-nonsense delivery has been instrumental in establishing Boston’s gritty, raw hip-hop style. Making standout appearances on Gang Starr albums, like “The Militia” off 1998’s Moment of Trut, Shug has shown unwavering commitment to authenticity and integrity in his craft, proving that Boston’s hip hop scene is steeped in tradition, yet not averse to innovation.

2. Ed O.G.

Discography: The Truth Hurts (2000), Wishful Thinking (2002), A Face In The Crowd (2011), Intelligence & Ignorance (2013), After All These Years (2014), FreEDOm (2017)

As one of Boston’s earliest and most influential rap figures, Ed O.G. has left an indelible mark on the city’s hip-hop scene. Bursting onto the scene in the late ’80s with his crew Da Bulldogs, his gritty, candid approach to rapping has been instrumental in defining Boston’s hip-hop identity. Renowned for tackling issues of social justice and urban life in his lyrics, Ed O.G. remains a leading light in Boston’s hip-hop lineage, inspiring countless artists with his authentic storytelling and unapologetic style. The legendary Boston MC is also responsible for one of the greatest rap songs about fatherhood — “Be a Father to Your Child.”

1. Guru

Discography: Guru’s Jazzmatazz, Vol. 1 (1993), Guru’s Jazzmatazz, Vol. 2: The New Reality (1995), Guru’s Jazzmatazz, Vol. 3: Streetsoul (2000), Baldhead Slick & da Click (2001), Version 7.0: The Street Scriptures (2005), Guru’s Jazzmatazz, Vol. 4: The Hip Hop Jazz Messenger: Back to the Future (2007), Guru 8.0: Lost and Found (2009)

At the apex of Boston’s hip hop hierarchy sits the legendary Guru. Born in Roxbury, Guru (an acronym for Gifted Unlimited Rhymes Universal) is globally renowned as one-half of the influential rap duo Gang Starr, with DJ Premier. As part of a rap act who helped to define ’90s East Coast rap, his lyricism, marked by an insightful blend of street wisdom and social consciousness, helped shape hip hop’s golden age and has inspired countless artists since. Guru’s Jazzmatazz series also highlighted his ability to blur genre lines and innovate within hip hop, further solidifying his status as not just Boston’s greatest MC, but one of jazz-rap’s timeless greats.

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